PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2010 February 1; 66(Pt 2): o284.
Published online 2010 January 9. doi:  10.1107/S160053680905507X
PMCID: PMC2979720

4-[4-(Piperidin-1-yl)piperidin-1-yl]benzonitrile

Abstract

In the title compound, C17H23N3, both piperidine rings adopt chair conformations. In the crystal packing, intermolecular C—H(...)N hydrogen bonds and C—H(...)π interactions are present.

Related literature

For general background, see: Pevarello et al. (2006 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-0o284-scheme1.jpg

Experimental

Crystal data

  • C17H23N3
  • M r = 269.38
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0o284-efi1.jpg
  • a = 10.090 (2) Å
  • b = 11.100 (2) Å
  • c = 13.446 (3) Å
  • β = 100.72 (3)°
  • V = 1479.7 (5) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.07 mm−1
  • T = 113 K
  • 0.26 × 0.25 × 0.20 mm

Data collection

  • Rigaku Saturn CCD area-detector diffractometer
  • Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 [triangle]) T min = 0.981, T max = 0.986
  • 11970 measured reflections
  • 3500 independent reflections
  • 2749 reflections with I > 2σ(I)
  • R int = 0.032

Refinement

  • R[F 2 > 2σ(F 2)] = 0.038
  • wR(F 2) = 0.111
  • S = 1.12
  • 3500 reflections
  • 182 parameters
  • H-atom parameters constrained
  • Δρmax = 0.27 e Å−3
  • Δρmin = −0.19 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2005 [triangle]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ChemBioDraw Ultra CambridgeSoft (2008 [triangle]); software used to prepare material for publication: SHELXL97.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680905507X/kp2240sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680905507X/kp2240Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

The authors thank Mr Zhi-Hua Mao of Sichuan University for the X-ray data collection.

supplementary crystallographic information

Comment

4-(4-(Piperidin-1-yl)piperidin-1-yl)benzonitrile are key intermediates which can be used to synthesize 3-aminopyrazole derivatives, which can be used as precursors for anticancer and anti-malarial agents. In the structure of the title molecule (Fig. 1) both piperidine rings are in a chair conformation. A crystal packing is dominated by van der Waals interactions (Fig. 2).

Experimental

A DMSO solution of 1-(piperidin-4-yl)piperidine (4.37 g, 0.01 mol) with 4-fluorobenzonitrile (1.21 g, 0.01 mol) was heated to reflux for 3 h, then water (50 ml) was added into the solution. The mixture was extracted with CH2Cl2. After the solvent was removed a red crystalline powder was obtained; its recrystallisation from a methanol solution after 5 days yielded single crystals.

Figures

Fig. 1.
The molecular structure of the title compound, with displacement ellipsoids drawn at the 30% probability level.
Fig. 2.
The crystal packing of I dominated by van der Waals interactions.

Crystal data

C17H23N3F(000) = 584
Mr = 269.38Dx = 1.209 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 4488 reflections
a = 10.090 (2) Åθ = 2.7–27.9°
b = 11.100 (2) ŵ = 0.07 mm1
c = 13.446 (3) ÅT = 113 K
β = 100.72 (3)°Block, red
V = 1479.7 (5) Å30.26 × 0.25 × 0.20 mm
Z = 4

Data collection

Rigaku Saturn CCD area-detector diffractometer3500 independent reflections
Radiation source: rotating anode2749 reflections with I > 2σ(I)
confocalRint = 0.032
Detector resolution: 7.31 pixels mm-1θmax = 27.9°, θmin = 2.8°
ω and [var phi] scansh = −13→10
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)k = −14→14
Tmin = 0.981, Tmax = 0.986l = −17→17
11970 measured reflections

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.038H-atom parameters constrained
wR(F2) = 0.111w = 1/[σ2(Fo2) + (0.0612P)2 + 0.0668P] where P = (Fo2 + 2Fc2)/3
S = 1.12(Δ/σ)max < 0.001
3500 reflectionsΔρmax = 0.27 e Å3
182 parametersΔρmin = −0.19 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.033 (7)

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
N10.19321 (8)0.59022 (8)0.73578 (6)0.0193 (2)
N20.26675 (8)0.49828 (7)0.43659 (6)0.0187 (2)
N30.48688 (9)0.35177 (8)0.00345 (7)0.0256 (2)
C10.21163 (10)0.49931 (10)0.81631 (8)0.0225 (2)
H1A0.30690.47270.83040.027*
H1B0.15470.42830.79340.027*
C20.17411 (11)0.54896 (10)0.91273 (8)0.0270 (3)
H2A0.23630.61540.93910.032*
H2B0.18390.48480.96470.032*
C30.02945 (11)0.59541 (11)0.89283 (9)0.0310 (3)
H3A−0.03390.52700.87680.037*
H3B0.01020.63600.95420.037*
C40.00956 (11)0.68349 (11)0.80492 (9)0.0307 (3)
H4A0.06380.75690.82490.037*
H4B−0.08650.70740.78810.037*
C50.05156 (10)0.62790 (11)0.71205 (8)0.0274 (3)
H5A−0.00620.55730.68940.033*
H5B0.03920.68750.65630.033*
C60.24849 (10)0.54949 (9)0.64737 (8)0.0182 (2)
H60.34480.52720.67330.022*
C70.18209 (10)0.43925 (9)0.59102 (8)0.0205 (2)
H7A0.18160.37210.63940.025*
H7B0.08730.45840.56080.025*
C80.25693 (10)0.40038 (9)0.50799 (8)0.0204 (2)
H8A0.34880.37340.53910.024*
H8B0.20930.33130.47080.024*
C90.32454 (11)0.60897 (9)0.48736 (8)0.0224 (2)
H9A0.32060.67420.43660.027*
H9B0.42060.59480.51720.027*
C100.25036 (11)0.64891 (9)0.56997 (8)0.0229 (2)
H10A0.15660.67110.53940.027*
H10B0.29510.72110.60420.027*
C110.31345 (9)0.46754 (9)0.34801 (7)0.0179 (2)
C120.32252 (10)0.55520 (9)0.27405 (8)0.0209 (2)
H120.29760.63600.28490.025*
C130.36689 (10)0.52613 (9)0.18606 (8)0.0212 (2)
H130.37270.58700.13740.025*
C140.40341 (10)0.40774 (9)0.16801 (8)0.0182 (2)
C150.39452 (10)0.31974 (9)0.24037 (8)0.0203 (2)
H150.41910.23900.22890.024*
C160.35023 (10)0.34886 (9)0.32857 (8)0.0205 (2)
H160.34450.28760.37700.025*
C170.45003 (10)0.37726 (9)0.07679 (8)0.0200 (2)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
N10.0189 (4)0.0234 (5)0.0162 (4)0.0020 (3)0.0049 (3)−0.0006 (3)
N20.0253 (4)0.0146 (4)0.0169 (4)−0.0026 (3)0.0060 (3)−0.0002 (3)
N30.0337 (5)0.0195 (5)0.0252 (5)−0.0013 (4)0.0101 (4)−0.0025 (4)
C10.0240 (5)0.0248 (5)0.0194 (5)0.0000 (4)0.0053 (4)0.0015 (4)
C20.0287 (6)0.0343 (6)0.0190 (6)−0.0034 (5)0.0071 (4)−0.0014 (5)
C30.0272 (6)0.0414 (7)0.0273 (6)−0.0046 (5)0.0127 (5)−0.0073 (5)
C40.0237 (5)0.0400 (7)0.0300 (6)0.0065 (5)0.0085 (5)−0.0051 (5)
C50.0215 (5)0.0370 (6)0.0237 (6)0.0071 (5)0.0044 (4)−0.0020 (5)
C60.0183 (5)0.0197 (5)0.0170 (5)0.0005 (4)0.0045 (4)−0.0008 (4)
C70.0226 (5)0.0200 (5)0.0196 (5)−0.0024 (4)0.0058 (4)0.0011 (4)
C80.0272 (5)0.0160 (5)0.0189 (5)−0.0022 (4)0.0069 (4)0.0008 (4)
C90.0287 (5)0.0187 (5)0.0210 (5)−0.0062 (4)0.0076 (4)−0.0031 (4)
C100.0315 (6)0.0177 (5)0.0212 (6)−0.0024 (4)0.0094 (4)−0.0023 (4)
C110.0178 (5)0.0183 (5)0.0170 (5)−0.0011 (4)0.0018 (4)−0.0009 (4)
C120.0263 (5)0.0161 (5)0.0209 (5)0.0028 (4)0.0059 (4)0.0000 (4)
C130.0268 (5)0.0187 (5)0.0185 (5)0.0012 (4)0.0054 (4)0.0027 (4)
C140.0196 (5)0.0181 (5)0.0171 (5)−0.0009 (4)0.0033 (4)−0.0014 (4)
C150.0238 (5)0.0164 (5)0.0205 (6)0.0007 (4)0.0033 (4)−0.0017 (4)
C160.0253 (5)0.0170 (5)0.0187 (5)−0.0007 (4)0.0031 (4)0.0011 (4)
C170.0236 (5)0.0145 (5)0.0216 (6)−0.0012 (4)0.0038 (4)0.0000 (4)

Geometric parameters (Å, °)

N1—C51.4663 (13)C6—H61.0000
N1—C11.4664 (13)C7—C81.5219 (14)
N1—C61.4749 (13)C7—H7A0.9900
N2—C111.4020 (13)C7—H7B0.9900
N2—C81.4656 (13)C8—H8A0.9900
N2—C91.4723 (13)C8—H8B0.9900
N3—C171.1520 (13)C9—C101.5164 (14)
C1—C21.5200 (14)C9—H9A0.9900
C1—H1A0.9900C9—H9B0.9900
C1—H1B0.9900C10—H10A0.9900
C2—C31.5241 (16)C10—H10B0.9900
C2—H2A0.9900C11—C161.4063 (14)
C2—H2B0.9900C11—C121.4064 (14)
C3—C41.5183 (17)C12—C131.3788 (14)
C3—H3A0.9900C12—H120.9500
C3—H3B0.9900C13—C141.3981 (14)
C4—C51.5220 (15)C13—H130.9500
C4—H4A0.9900C14—C151.3933 (14)
C4—H4B0.9900C14—C171.4335 (14)
C5—H5A0.9900C15—C161.3811 (14)
C5—H5B0.9900C15—H150.9500
C6—C101.5195 (14)C16—H160.9500
C6—C71.5269 (14)
C5—N1—C1109.98 (8)C8—C7—H7A109.4
C5—N1—C6114.29 (8)C6—C7—H7A109.4
C1—N1—C6111.67 (8)C8—C7—H7B109.4
C11—N2—C8116.77 (8)C6—C7—H7B109.4
C11—N2—C9115.49 (8)H7A—C7—H7B108.0
C8—N2—C9112.59 (8)N2—C8—C7111.93 (8)
N1—C1—C2111.27 (9)N2—C8—H8A109.2
N1—C1—H1A109.4C7—C8—H8A109.2
C2—C1—H1A109.4N2—C8—H8B109.2
N1—C1—H1B109.4C7—C8—H8B109.2
C2—C1—H1B109.4H8A—C8—H8B107.9
H1A—C1—H1B108.0N2—C9—C10112.14 (8)
C1—C2—C3110.81 (9)N2—C9—H9A109.2
C1—C2—H2A109.5C10—C9—H9A109.2
C3—C2—H2A109.5N2—C9—H9B109.2
C1—C2—H2B109.5C10—C9—H9B109.2
C3—C2—H2B109.5H9A—C9—H9B107.9
H2A—C2—H2B108.1C9—C10—C6111.10 (8)
C4—C3—C2109.76 (9)C9—C10—H10A109.4
C4—C3—H3A109.7C6—C10—H10A109.4
C2—C3—H3A109.7C9—C10—H10B109.4
C4—C3—H3B109.7C6—C10—H10B109.4
C2—C3—H3B109.7H10A—C10—H10B108.0
H3A—C3—H3B108.2N2—C11—C16121.86 (9)
C3—C4—C5111.16 (10)N2—C11—C12120.57 (9)
C3—C4—H4A109.4C16—C11—C12117.55 (9)
C5—C4—H4A109.4C13—C12—C11121.27 (9)
C3—C4—H4B109.4C13—C12—H12119.4
C5—C4—H4B109.4C11—C12—H12119.4
H4A—C4—H4B108.0C12—C13—C14120.46 (9)
N1—C5—C4110.24 (9)C12—C13—H13119.8
N1—C5—H5A109.6C14—C13—H13119.8
C4—C5—H5A109.6C15—C14—C13118.98 (9)
N1—C5—H5B109.6C15—C14—C17120.39 (9)
C4—C5—H5B109.6C13—C14—C17120.63 (9)
H5A—C5—H5B108.1C16—C15—C14120.57 (9)
N1—C6—C10112.59 (8)C16—C15—H15119.7
N1—C6—C7116.67 (8)C14—C15—H15119.7
C10—C6—C7107.60 (8)C15—C16—C11121.17 (9)
N1—C6—H6106.4C15—C16—H16119.4
C10—C6—H6106.4C11—C16—H16119.4
C7—C6—H6106.4N3—C17—C14179.37 (11)
C8—C7—C6111.06 (8)
C5—N1—C1—C2−60.67 (11)N2—C9—C10—C656.38 (12)
C6—N1—C1—C2171.35 (8)N1—C6—C10—C9172.41 (8)
N1—C1—C2—C356.80 (12)C7—C6—C10—C9−57.65 (11)
C1—C2—C3—C4−52.73 (12)C8—N2—C11—C16−0.48 (13)
C2—C3—C4—C553.76 (12)C9—N2—C11—C16135.34 (10)
C1—N1—C5—C460.92 (12)C8—N2—C11—C12178.25 (9)
C6—N1—C5—C4−172.56 (9)C9—N2—C11—C12−45.93 (12)
C3—C4—C5—N1−58.25 (12)N2—C11—C12—C13−179.30 (9)
C5—N1—C6—C1063.26 (11)C16—C11—C12—C13−0.52 (14)
C1—N1—C6—C10−171.10 (8)C11—C12—C13—C140.37 (15)
C5—N1—C6—C7−61.87 (12)C12—C13—C14—C15−0.13 (15)
C1—N1—C6—C763.77 (11)C12—C13—C14—C17−179.78 (9)
N1—C6—C7—C8−174.76 (8)C13—C14—C15—C160.05 (15)
C10—C6—C7—C857.63 (11)C17—C14—C15—C16179.70 (9)
C11—N2—C8—C7−169.71 (8)C14—C15—C16—C11−0.21 (15)
C9—N2—C8—C753.24 (11)N2—C11—C16—C15179.21 (9)
C6—C7—C8—N2−56.30 (11)C12—C11—C16—C150.44 (15)
C11—N2—C9—C10169.02 (8)C15—C14—C17—N338 (9)
C8—N2—C9—C10−53.35 (11)C13—C14—C17—N3−142 (9)

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C11–C16 ring.
D—H···AD—HH···AD···AD—H···A
C6—H6···Cgi1.002.993.9363 (14)158
C16—H16···N3ii0.952.543.3442 (16)143

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, −y+1/2, z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: KP2240).

References

  • CambridgeSoft (2008). ChemBioDraw Ultra CambridgeSoft, England.
  • Pevarello, P., Fancelli, D., Vulpetti, A., Amici, R., Villa, M., Pittalà, V., Vianello, P., Cameron, A., Ciomei, M., Mercurio, C., Bischoff, J. R., Roletto, F., Varasi, M. & Brasca, M. G. (2006). Bioorg. Med. Chem. Lett.16, 1084–1090. [PubMed]
  • Rigaku/MSC (2005). CrystalClear Rigaku/MSC, The Woodlands, Texas, USA.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography